Composition and cured product

Abstract

To provide a composition capable of yielding a cured product exhibiting a high refractive index, a low dielectric constant, a low dielectric loss tangent, and high toughness.SOLUTION: The composition comprises a compound represented by formula (A) and a compound represented by formula (B), where the content of the compound represented by formula (A) is 60-95 mass% relative to the total amount of the compounds represented by formulas (A) and (B), and the content of the compound represented by formula (B) is 5-40 mass% relative to the total amount of the compounds represented by formulas (A) and (B).SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a composition and a cured product. [Background technology]

[0002] Energy ray or ultraviolet curable resins have a high curing rate with low energy compared to thermally polymerizable resins, and are generally solvent-free and easy to work with, so energy ray or ultraviolet curing technology is an important environmentally friendly technology. The energy ray or ultraviolet curable resins are used in a variety of applications, for example, as optical materials such as hard coating agents, antireflection agents, adhesives for displays, and sealants. The energy ray or ultraviolet curable resin is generally obtained by polymerizing raw materials such as monomers and oligomers, and for example, a composition containing the raw materials is often used.

[0003] Patent Document 1 discloses the above composition containing a specific compound. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Application Laid-Open No. 2012-082387 Summary of the Invention [Problem to be solved by the invention]

[0005] The present inventors have studied the cured product (resin) obtained by curing the composition described in Patent Document 1 and have found that there is room for improvement in at least one of the refractive index, dielectric constant, dielectric loss tangent, and toughness.

[0006] Therefore, an object of the present invention is to provide a composition that can give a cured product that exhibits a high refractive index, a low dielectric constant, a low dielectric loss tangent, and high toughness. [Means for solving the problem]

[0007] As a result of extensive research, the present inventors have found that the above object can be achieved by employing the following configuration, and have completed the present invention.

[0008] [1] A compound represented by the formula (A) described below and a compound represented by the formula (B) described below, the content of the compound represented by the formula (A) is 60 to 95 mass% relative to the total amount of the compound represented by the formula (A) and the compound represented by the formula (B); A composition, wherein the content of the compound represented by the formula (B) is 5 to 40 mass % relative to the total amount of the compound represented by the formula (A) and the compound represented by the formula (B). [2] A cured product obtained by curing the composition described in [1]. [Effects of the Invention]

[0009] According to the present invention, it is possible to provide a composition that can give a cured product that exhibits a high refractive index, a low dielectric constant, a low dielectric loss tangent, and high toughness. DETAILED DESCRIPTION OF THE INVENTION

[0010] The composition of the present invention will now be described.

[0011] [Composition] The composition of the present invention (hereinafter also simply referred to as "composition") contains a predetermined amount of a compound represented by formula (A) and a predetermined amount of a compound represented by formula (B).

[0012] <Compound represented by formula (A)> The composition comprises a compound represented by formula (A). The content of the compound represented by formula (A) is 60 to 95 mass%, or may be 65 to 95 mass%, or further may be 80 to 95 mass%, relative to the total amount (100 mass%) of the compound represented by formula (A) and the compound represented by formula (B).

[0013] [ka]

[0014] In formula (A), R 1 represents a hydrogen atom or a methyl group.

[0015] Examples of the compound represented by formula (A) include 1-naphthylmethyl acrylate and 1-naphthylmethyl methacrylate.

[0016] The compound represented by formula (A) may be used alone or in combination of two or more. The content of the compound represented by formula (A) may be 55 to 95 mass % or 60 to 95 mass % relative to the total mass of the composition.

[0017] <Compound represented by formula (B)> The composition comprises a compound represented by formula (B). The content of the compound represented by formula (B) is 5 to 40 mass %, may be 5 to 35 mass %, or may further be 5 to 20 mass %, relative to the total amount (100 mass %) of the compound represented by formula (A) and the compound represented by formula (B).

[0018] [ka]

[0019] In formula (B), R 1 and R 2 each independently represents a hydrogen atom or a methyl group.

[0020] Examples of the compound represented by formula (B) include 4,4'-bisacryloylmethylbiphenyl and 4,4'-bismethacryloylmethylbiphenyl.

[0021] The compound represented by formula (B) may be used alone or in combination of two or more. The content of the compound represented by formula (B) may be 1 to 40 mass %, or 1 to 30 mass %, relative to the total mass of the composition.

[0022] The total content of the compound represented by formula (A) and the compound represented by formula (B) is preferably 95 to 100 mass %, more preferably 97 to 100 mass %, based on the total mass (100 mass %) of the composition.

[0023] <Polymerization initiator> The composition may also include a polymerization initiator. The polymerization initiator is not particularly limited as long as it activates the olefin moiety of the compound represented by the above formula (A) and the compound represented by the above formula (B), and known polymerization initiators can be used. Examples of the polymerization initiator include: a thermally decomposable radical generator having an azo structure; an intramolecular cleavage polymerization initiator such as a hydroxyalkylphenone, an acylphosphine oxide, or an oxime ester; an intramolecular hydrogen abstraction polymerization initiator; a Bronsted acid generating polymerization initiator; and an onium salt initiator such as an iodonium salt, a sulfonium salt, a selenonium salt, a phosphonium salt, a diazonium salt, or an antimony hexafluoride.

[0024] The polymerization initiator may be used alone or in combination of two or more. The content of the polymerization initiator is preferably 0.3 to 5.0 mass %, more preferably 1.0 to 3.0 mass %, relative to the total amount (100 mass %) of the compound represented by formula (A) and the compound represented by formula (B).

[0025] <Other ingredients> The composition may contain other ingredients. Examples of other components include polymerizable olefins other than the compound represented by formula (A) and the compound represented by formula (B); cyclic ethers such as epoxy and oxetane; organopolysiloxane; adhesion improvers that improve adhesion to substrates; leveling agents; antistatic agents; high flexibility materials; flame retardants; antifoaming agents; pigments; fillers; and talc.

[0026] <Preparation method> The method for preparing the composition is not particularly limited. Examples of a method for preparing the composition include a method of mixing a compound represented by formula (A) and a compound represented by formula (B), and, if necessary, further mixing at least one of a polymerization initiator and other components.

[0027] [Cured product] The cured product is not particularly limited as long as it is obtained by curing the composition. The cured product is preferably a cured product obtained by applying the composition to a substrate to form a coating film and curing the coating film, or a cured product obtained by pouring the composition into a mold and curing the composition.

[0028] The substrate may be in the form of, for example, a film, a sheet, or a molded product. Examples of materials for the substrate include metals such as steel, copper, and aluminum; synthetic resins; glass; and carbon fiber, and the material is appropriately selected depending on the application. Examples of methods for applying the composition include roll coating, gravure coating, die coating, wire doctor coating, spraying, mist spraying, dipping, and ink jetting.

[0029] The coating film can be cured by heating or ultraviolet irradiation, for example. For example, when using a high-pressure mercury lamp (80 W / cm), the coating film can be cured by irradiating the object with the high-pressure mercury lamp for 0.01 to 30 seconds from a position where the distance between the lamp and the object is 5 to 20 cm. Examples of the device used for heating (heating device) include a hot air dryer, a far-infrared heater, and a heating furnace. Examples of light sources for ultraviolet irradiation devices include high-pressure mercury lamps, medium-pressure mercury lamps, low-pressure mercury lamps, metal halide lamps, mercury arc lamps, and light-emitting diodes.

[0030] <Application> The use of the composition is not particularly limited, and it can be used in a variety of fields. The composition can be used, for example, as a diluent. A cured product obtained by curing the composition can be used, for example, as a hard coat layer or adhesive layer for displays, sensor lenses, etc., a protective coating agent for metals, plastics, etc., an antistatic layer, an antiglare layer, a polarizing layer, a retardation layer, a circularly polarizing layer, or an antireflection layer. [Example]

[0031] The present invention will be specifically described below with reference to examples, but the present invention is not limited to the examples described below.

[0032] [Preparation of Composition] Predetermined amounts of various components were placed in a light-shielded glass bottle as shown in the table below, and 3 mass % of Irgacure 184 (manufactured by IGM Resins BV) was further added relative to the total amount (100 mass %) of the compound represented by formula (A), the compound represented by formula (B), and other compounds shown in the table. The mixture was mixed for 30 minutes in a shaker with the ambient temperature controlled at 23±1°C to obtain each composition.

[0033] [evaluation] <Refractive index> The resulting compositions were placed in silicone molds and cured by UV light (integrated light dose 2000-4000 mJ / cm 2 ) and molded into a rectangular parallelepiped shape measuring 20 mm long x 8 mm wide x 5 mm thick to obtain test pieces of each cured product (resin). The refractive index of each obtained test piece was measured using a multi-wavelength Abbe refractometer DR-M2 (manufactured by Atago Co., Ltd.) with intermediate liquid LJ (nD = 1.80, manufactured by Atago Co., Ltd.). The measurement wavelength was 589 nm (D). The refractive index is preferably 1.615 or higher. In the tables shown later, for comparative examples in which the evaluation result of the refractive index is marked as "measurable," this indicates that the obtained test specimen was brittle, and cracks occurred when the test specimen was set for measurement, making it impossible to measure.

[0034] <Relative permittivity and dielectric loss tangent> The resulting compositions were placed in aluminum containers with a diameter of 40 mm and a height of 6 mm and cured with ultraviolet light (integrated light dose of 2000 to 4000 mJ / cm). 2After the curing, the aluminum container was removed to obtain each cured product. The bottom surface of each cured product was sanded with sandpaper to create a flat surface (measurement surface), which was then washed with ethanol and left to stand at 23°C and 50% Rh (relative humidity) for 24 hours to obtain a test specimen. The relative permittivity and dielectric loss tangent of the test specimens at 9.4 GHz were measured using a coaxial resonator (manufactured by AET). The relative permittivity is preferably 3.000 or less, more preferably 2.900 or less. The dielectric loss tangent is preferably 0.010 or less, more preferably 0.009 or less, and most preferably 0.005 or less. In the tables shown later, for the comparative examples in which the evaluation results of the dielectric constant and the dielectric loss tangent are marked as "measurable," this indicates that when the bottom surface of the cured product was scraped with sandpaper, the cured product became brittle and crumbled, making it impossible to prepare a measurement surface, and therefore the dielectric constant and the dielectric loss tangent of the cured product could not be measured.

[0035] <Toughness> The resulting compositions were placed in aluminum containers with a diameter of 40 mm and a height of 5 mm and cured with ultraviolet light (integrated light dose of 2000 to 4000 mJ / cm). 2 After the test, the aluminum container was peeled off to obtain each cured product. During the peeling operation, the presence or absence of cracks was visually confirmed, and the toughness was evaluated according to the following evaluation criteria. "○": No cracks were found. "X": Cracks were present.

[0036] The following table shows the compositions of the examples and comparative examples and the evaluation results. In the table, the contents of the compound represented by formula (A), the compound represented by formula (B), and the other compounds are the contents (% by mass) relative to the total amount (100% by mass) of the compound represented by formula (A), the compound represented by formula (B), and the other compounds. When the composition does not contain other compounds, the content of each of the above compounds is synonymous with the content (% by mass) relative to the total amount (100% by mass) of the compound represented by formula (A) and the compound represented by formula (B). In addition, in the table, for Comparative Examples 17 and 18, the composition was cured by ultraviolet light (integrated light dose 2000 to 4000 mJ / cm 2) was carried out, no cured product was obtained, and therefore no evaluation could be carried out. In Comparative Examples 19 and 20, 4,4'-DVBP was not completely dissolved in the composition, and therefore UV curing of the composition could not be carried out, and therefore no evaluation could be carried out.

[0037] [Table 1]

[0038] [Table 2]

[0039] [Table 3]

[0040] [Table 4]

[0041] The compound names corresponding to the abbreviations of each compound in the above table are shown below, and the structural formulas of each compound are shown in Table 5 below. 1-NMA: 1-naphthyl methyl acrylate, manufactured by JFE Chemical Corporation 1-NMMA: 1-naphthylmethyl methacrylate, manufactured by JFE Chemical Corporation DABP: 4,4'-bisacryloylmethylbiphenyl, manufactured by JFE Chemical Corporation DMABP: 4,4'-bismethacryloylmethylbiphenyl, manufactured by JFE Chemical Corporation PEA: Phenoxyethyl acrylate, manufactured by Tokyo Chemical Industry Co., Ltd. IBA: Isobornyl acrylate, manufactured by Tokyo Chemical Industry Co., Ltd. BAH: Bisacryloyloxyhexane, manufactured by Tokyo Chemical Industry Co., Ltd. DCP-DMA: Tricyclo[5.2.1.0 2,6] Decane dimethanol diacrylate, Sigma-Aldridge OPBA: o-phenylbenzyl acrylate, manufactured by JFE Chemical Corporation OPPEA: o-phenylphenoxyethyl acrylate, manufactured by Tokyo Chemical Industry Co., Ltd. 1-VN: 1-vinylnaphthalene, manufactured by JFE Chemical Corporation 4,4'-DVBP: 4,4'-divinylbiphenyl, manufactured by JFE Chemical Corporation

[0042] [Table 5]

[0043] As shown in the above table, it was confirmed that the cured products obtained using the compositions of the examples exhibited a high refractive index, a low relative dielectric constant, a low dielectric loss tangent, and high toughness.

Claims

1. A compound represented by formula (A) and a compound represented by formula (B), the content of the compound represented by formula (A) is 60 to 95 mass% based on the total amount of the compound represented by formula (A) and the compound represented by formula (B), The content of the compound represented by formula (B) is 5 to 40 mass% based on the total amount of the compound represented by formula (A) and the compound represented by formula (B). 【Chemical 1】 In formula (A) and formula (B), R １ ~R ３ each independently represents a hydrogen atom or a methyl group.

2. A cured product obtained by curing the composition according to claim 1.

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